Motivation – Intelligent software tools face substantial obstacles to adoption, because of their complexity and lack of transparency. Research Approach – We describe the Experiential User Guide for intelligent software systems, which aims to compress critical challenges users discover along the pathway to expertise. Design– The EUG uses vignettes to illustrate learning challenges, employing examples of how the tool can be used successfully, and examples of its limitations, boundary conditions, and the common errors made by users of the tool. Research limitations/Implications. The EUG focuses on advanced concepts of operation, as these are areas that can especially benefit from experiential training. Originality/Value – The EUG shows how software is used in situ, rather than the more typical toolcentered approach describing the different functions of the software system. Take away message – The EUG is a new approach to help users of intelligent software tools become experts faster and more systematically.